HRP20131067T1 - Arilcikloheksileteri od dihidrotetraazabenzoazulena za primjenu kao antagonista receptora vazopresina v1a - Google Patents
Arilcikloheksileteri od dihidrotetraazabenzoazulena za primjenu kao antagonista receptora vazopresina v1a Download PDFInfo
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- HRP20131067T1 HRP20131067T1 HRP20131067AT HRP20131067T HRP20131067T1 HR P20131067 T1 HRP20131067 T1 HR P20131067T1 HR P20131067A T HRP20131067A T HR P20131067AT HR P20131067 T HRP20131067 T HR P20131067T HR P20131067 T1 HRP20131067 T1 HR P20131067T1
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- Croatia
- Prior art keywords
- chloro
- tetraaza
- cyclohexyl
- trans
- dihydro
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- 102000004136 Vasopressin Receptors Human genes 0.000 title 1
- 108090000643 Vasopressin Receptors Proteins 0.000 title 1
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 23
- -1 3-cyano-phenyl Chemical group 0.000 claims 19
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- GMPZPHGHNDMRKL-RZDIXWSQSA-N O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C)C1=CC=CC=N1 Chemical compound O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C)C1=CC=CC=N1 GMPZPHGHNDMRKL-RZDIXWSQSA-N 0.000 claims 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- JKYMCTSCSIGOHG-UKIBZPOASA-N CN1Cc2nnc([C@H]3CC[C@@H](CC3)Oc3ccccc3)n2-c2ccc(Cl)cc2C1 Chemical compound CN1Cc2nnc([C@H]3CC[C@@H](CC3)Oc3ccccc3)n2-c2ccc(Cl)cc2C1 JKYMCTSCSIGOHG-UKIBZPOASA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- WCLNITYOMFLRKI-UHFFFAOYSA-N 1-[8-chloro-1-(4-phenoxycyclohexyl)-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-5-yl]-2-(dimethylamino)ethanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C(=O)CN(C)C)CC2=NN=C1C(CC1)CCC1OC1=CC=CC=C1 WCLNITYOMFLRKI-UHFFFAOYSA-N 0.000 claims 1
- PZQAIPWCFHKCFU-UHFFFAOYSA-N 1-[8-chloro-1-(4-phenoxycyclohexyl)-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-5-yl]ethanone Chemical compound N12C3=CC=C(Cl)C=C3CN(C(=O)C)CC2=NN=C1C(CC1)CCC1OC1=CC=CC=C1 PZQAIPWCFHKCFU-UHFFFAOYSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- DIJCZNXKWZBPPS-UHFFFAOYSA-N 8-chloro-5-methylsulfonyl-1-(4-phenoxycyclohexyl)-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound N12C3=CC=C(Cl)C=C3CN(S(=O)(=O)C)CC2=NN=C1C(CC1)CCC1OC1=CC=CC=C1 DIJCZNXKWZBPPS-UHFFFAOYSA-N 0.000 claims 1
- WNZQFVSIYYJOIN-UHFFFAOYSA-N 8-chloro-n,n-dimethyl-1-(4-phenoxycyclohexyl)-4,6-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-5-sulfonamide Chemical compound N12C3=CC=C(Cl)C=C3CN(S(=O)(=O)N(C)C)CC2=NN=C1C(CC1)CCC1OC1=CC=CC=C1 WNZQFVSIYYJOIN-UHFFFAOYSA-N 0.000 claims 1
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- JCRFOOMNRNMHGB-CYWCHRQTSA-N O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C(=O)OC(C)(C)C)C1=CC=CC(Cl)=C1 Chemical compound O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C(=O)OC(C)(C)C)C1=CC=CC(Cl)=C1 JCRFOOMNRNMHGB-CYWCHRQTSA-N 0.000 claims 1
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- DRVPVMXJZRGZFS-QUWSVYMGSA-N O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C)C1=CC(F)=CC(F)=C1 Chemical compound O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C)C1=CC(F)=CC(F)=C1 DRVPVMXJZRGZFS-QUWSVYMGSA-N 0.000 claims 1
- TUUTUWITTXYIBR-RHDGDCLCSA-N O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C)C1=CC=C(F)C=C1 Chemical compound O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C)C1=CC=C(F)C=C1 TUUTUWITTXYIBR-RHDGDCLCSA-N 0.000 claims 1
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- NBNWYACBLIJZEU-RHDGDCLCSA-N O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C)C1=CC=CC(Cl)=C1 Chemical compound O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)C)C1=CC=CC(Cl)=C1 NBNWYACBLIJZEU-RHDGDCLCSA-N 0.000 claims 1
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- APHONEKEHMGFSU-CYWCHRQTSA-N O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)CCO)C1=CC=CC=C1 Chemical compound O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(Cl)=CC=C3N21)CCO)C1=CC=CC=C1 APHONEKEHMGFSU-CYWCHRQTSA-N 0.000 claims 1
- ZPTKMLWBOSMALM-LBZQVFOQSA-N O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(F)=CC=C3N21)C(=O)OC(C)(C)C)C1=CC=CC=C1 Chemical compound O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(F)=CC=C3N21)C(=O)OC(C)(C)C)C1=CC=CC=C1 ZPTKMLWBOSMALM-LBZQVFOQSA-N 0.000 claims 1
- IIUPKCDYMXHNNV-UKIBZPOASA-N O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(F)=CC=C3N21)C)C1=CC=CC=C1 Chemical compound O([C@H]1CC[C@@H](CC1)C1=NN=C2CN(CC3=CC(F)=CC=C3N21)C)C1=CC=CC=C1 IIUPKCDYMXHNNV-UKIBZPOASA-N 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims 1
- 102000002852 Vasopressins Human genes 0.000 claims 1
- 108010004977 Vasopressins Proteins 0.000 claims 1
- 230000016571 aggressive behavior Effects 0.000 claims 1
- 208000012761 aggressive behavior Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000007882 cirrhosis Effects 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000001788 irregular Effects 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
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- Neurosurgery (AREA)
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- Urology & Nephrology (AREA)
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- Pain & Pain Management (AREA)
- Gastroenterology & Hepatology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08170188 | 2008-11-28 | ||
| PCT/EP2009/065354 WO2010060836A1 (en) | 2008-11-28 | 2009-11-18 | Arylcyclohexylethers of dihydrotetraazabenzoazulenes for use as vasopressin via receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20131067T1 true HRP20131067T1 (hr) | 2013-12-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20131067AT HRP20131067T1 (hr) | 2008-11-28 | 2013-11-08 | Arilcikloheksileteri od dihidrotetraazabenzoazulena za primjenu kao antagonista receptora vazopresina v1a |
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| EP (1) | EP2370441B1 (pl) |
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| BR (1) | BRPI0922303B1 (pl) |
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| CO (1) | CO6341478A2 (pl) |
| CR (1) | CR20110220A (pl) |
| CY (1) | CY1115435T1 (pl) |
| DK (1) | DK2370441T3 (pl) |
| EC (1) | ECSP11011089A (pl) |
| ES (1) | ES2431279T3 (pl) |
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| HR (1) | HRP20131067T1 (pl) |
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| MX (1) | MX2011005596A (pl) |
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| NZ (1) | NZ592076A (pl) |
| PE (1) | PE20110582A1 (pl) |
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| UA (1) | UA103504C2 (pl) |
| WO (1) | WO2010060836A1 (pl) |
| ZA (1) | ZA201103419B (pl) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011143366A1 (en) * | 2010-05-13 | 2011-11-17 | Amgen Inc. | Heteroaryloxycarbocyclyl compounds as pde10 inhibitors |
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